Holiday rentals in Castlewood

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Top-rated holiday rentals in Castlewood

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Top guest favourite

Barn in Watertown

4.95 out of 5 average rating, 272 reviews

Silverstar Barn

Silverstar Barn is located on 10 acres just 3 miles south of Watertown on blacktop road. It is approximately 150 feet from our residence. Rest assure that you will be left alone to enjoy your extended or weekend getaway. We have just completed remodeling the other half of the barn turning it onto another rental. Silver star Stables has it's own entrance and both units have there own patio doors, one facing east, the other west for private outdoor seating. Both units have there own grill as well.

Guest favourite

Cabin in Watertown

4.92 out of 5 average rating, 226 reviews

Lakefront Cozy Cabin - Watertown Kampeska

This lakefront cabin is freshly remodeled in 2013, and includes all the amenities! Warm colors, dog friendly, plenty of parking, great for a summer getaway with the crew, or a winter getaway with the family. Room to beach or anchor a boat, and if the lake is frozen, perfect location to wake right up and head out on the ice to fish. Kayaks available for use! Bedrooms sleep 2 people each, and there is a loveseat and couch in the living room. Two cots also available to sleep additional people.

Top guest favourite

Farm stay in Hayti

5 out of 5 average rating, 23 reviews

Rustic Retreat

Relax at this unique & tranquil barn loft. The main loft features a large living area w/ additional sleeping options, TV & swing. The kitchen & bath are also on this level. An additional half loft holds 2 bedrooms. We’re secluded on 160@ of conservation habitat in the heart of prairie pothole region. There are many public hunting/fishing areas nearby. We offer places to clean your game/fish as well as a fire pit & seating to enjoy the prairie sunset. Dogs welcome w/ notice. RV hookup available.

Top guest favourite

Flat in Watertown

5 out of 5 average rating, 15 reviews

Restful Retreat * 2nd floor apt

Lovely 2nd floor apartment, spotlessly clean and tastefully decorated! We're located right in the center of town, with private driveway parking and close to everything. Full kitchen with dishes, cookware, all appliances. Large bedroom has queen-sized bed, small bedroom has twin bed; twin air mattress available. Living room has three recliners, smart TV, high-speed wifi, and comfy nook with toys for the kids. Private entrance. Patio and gas grill are shared with the owners and are yours to use!

Guest favourite

Home in Watertown

4.92 out of 5 average rating, 12 reviews

Cozy 2-Bed, 2-Bath Home

Located in a quiet neighborhood near Lake Area College, this split-level duplex unit features 2 bedrooms, 2 bathrooms, and an additional room in the basement. Each bedroom can sleep two; there is a sofa bed in the bonus room and a couch in the living room to sleep additional people. Each bedroom has a queen bed and closet space. The dining room includes a dinner table, which is expandable. If booked for over 7 days, we offer a 15% discount. If booked for over 28 days, we offer a 35% discount.

Top guest favourite

Guest suite in Astoria

5 out of 5 average rating, 50 reviews

Sokota Suite in the Country

Our suite is located on our peaceful farm.We are just a 10 minute drive to 2 lakes, Lake Cochrane, and Lake Hendricks and a 2 minute drive to Fish Lake. We have 5 different golf courses within a 20 minute drive and they are all open to the public ! We are located 30 miles, an easy country drive, to Brookings/SDSU.Our farm is on a paved highway and you can enjoy a quiet walk to a beautiful country church just 1/8 mile away. We have an unattached garage that you can have access to use for a fee,

Top guest favourite

Cabin in Estelline

4.97 out of 5 average rating, 116 reviews

3-Bedroom House on Lake Poinsett

Escape to the lake! Come out and relax with family and friends! Year-round enjoyment - swimming, open water fishing, kayaking, ice fishing, snowmobiling and more! You will have private access to the lake with a dock. The dock is generally in the water May through Labor Day. Note: There are several stairs required to get down to the dock. Boat ramp and shared public beach nearby. Inquire about floating water mat if interested (additional cost).

Guest favourite

Cabin in Estelline

4.91 out of 5 average rating, 132 reviews

Malomar on beautiful Lake Poinsett!

Enjoy lakeside living on beautiful Lake Poinsett, SD. Spacious kitchen/great room with wood fireplace that opens to 12x24 foot patio-balcony with propane grill, table & chairs, and spectacular view of the lake. Sleeping for 10 makes it the perfect place for the whole family and fishing/hunting groups! Minutes from boat ramp, dining, groceries, golf & Lake Poinsett State Recreation Area. Keyless entry makes check-in a snap!

Guest favourite

Home in Estelline

4.98 out of 5 average rating, 51 reviews

Charming Lake House, Hot Tub, Sauna, Private Dock

Welcome to Your Perfect Lakeside Retreat! Nestled on the serene shores of Lake Poinsett, SD, this charming lake house offers the ultimate getaway for families and couples alike. With 3 cozy bedrooms and 1 modern bathroom, you'll find everything you need for a relaxing and memorable stay. Enjoy breathtaking lake views from the private dock, unwind in the hot tub, or warm up in the sauna after a day of outdoor adventure.

Top guest favourite

Guest suite in Hayti

4.97 out of 5 average rating, 154 reviews

Salt and Light Retreat~ Overnight Stays - rural SD

Relax and get away from it all! A place to Literally UNPLUG from the world! A bit of a drive out, enjoying the farmlands you will find our Salt and Light Retreat for overnight stays. Private entry, garage parking, clean and comfy! Complimentary breakfast & full time coffee bar available We are not allowing pets at this time. Perhaps kenneled hunting dogs may work out Fishing trip? Boat parking available

Top guest favourite

Guest house in Dawson

5 out of 5 average rating, 72 reviews

The Loft

Come enjoy The Loft, a private space located above a detached garage with its own entrance. Appreciate the high end appliances and sunken shower big enough for two before falling into a cozy leather couch. This space provides a convenient location perfect for a solo traveler or a couple looking for a clean, comfortable, and stylish place to stay.

Top guest favourite

Guest suite in Watertown

4.97 out of 5 average rating, 114 reviews

Kampeska Lakefront Cottage

You will have access to one side of this lakefront duplex located directly on the lake. This property has two bedrooms, one bathroom, a washer and dryer as well as a fully furnished kitchen. This is the perfect getaway to enjoy the beautiful Lake Kampeska. Bonus: Enjoy a massage in your very own massage chair located in one of the bedrooms.

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Popular amenities for Castlewood holiday rentals

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Other great holiday rentals in Castlewood

Guest favourite

Cabin in Castlewood

4.85 out of 5 average rating, 33 reviews

Lakation Lake Poinsett Dock! 2 bed & bath

EmilyRating, 5 stars12 months ago

We had a great time! It is a beautiful property! They had all the essentials in the house, which we really appreciated. She was quick to respond to anything we needed. We had so fun making fires and playing in the water. We also loved that we could bring our pup with us. 10/10 🎉🙂

Guest favourite

Home in Watertown

4.85 out of 5 average rating, 13 reviews

It is a very nice 3 bedroom place!

JamesRating, 5 stars1 month ago

Stayed here while working in the area. Was quite happy with our stay and would stay here again.

Cabin in Lake Norden

4.51 out of 5 average rating, 90 reviews

Chic & Cozy Cabin with Private Hot Tub & Beach!

AlexanderRating, 5 stars1 month ago

We had an excellent stay at this chic and cozy home on the lake. The views and morning sunrises were incredible and host was responsive and helpful. Looking forward to visiting again sometime.

Top guest favourite

Home in Henry

5 out of 5 average rating, 9 reviews

M & M Hideaways

BaileyRating, 5 stars1 week ago

Melissa was responsive regarding our last minute booking. This is clearly a new Airbnb and is in a peaceful area. It met our expectations and would be perfect for a group hunting. I would recommend Melissa and her properties to others.

Guest favourite

Home in Watertown

4.91 out of 5 average rating, 11 reviews

Dad’s Place

MichelleRating, 5 stars1 week ago

Great place to stay easy access, great parking. affordable, clean and enough space for 2 small families or 1 larger family. We came for a basketball tournament so it was 2 moms and 3 kids. So much better than a hotel with tight space.

Top guest favourite

Campervan/Motorhome in Bradley

5 out of 5 average rating, 6 reviews

Indian Springs Glamping

BenRating, 5 stars7 months ago

Great place for us to stay for a long weekend of hunting. Comfortable for the 3 of us with everything we needed. Thanks!

Guest favourite

Farm stay in Estelline

4.88 out of 5 average rating, 116 reviews

A Taste of Farm Living

JoshRating, 5 stars1 month ago

Kristy, you rock and we’re awesome to talk to and do business with. We appreciate your family’s hospitality and willingness to have us as guests. We definitely are going to hit you up next time we are working in town!

Guest favourite